4412. Germine
Nomenclature
CAS number: 508-65-6
(3β,4α,7α,15α,16β)-4,9-Epoxycevane-3,4,7,14,15,16,20-heptol. C27H43NO8; mol wt 509.63.
C 63.63%, H 8.50%, N 2.75%, O 25.12%.
Description and references
Alkamine present in many polyester alkaloids which occur in Veratrum and Zygadenus species. Isoln: Poethke, Pharm. Monatsh. 18, 77 (1937); idem, Arch. Pharm. 275, 571 (1937); Seiferle et al., J. Econ. Entomol. 35, 35 (1942); Klohs et al., J. Am. Chem. Soc. 75, 4925 (1953); Kupchan, Deliwala, ibid. 76, 5545 (1954); Myers et al., ibid. 77, 3348 (1955); 78, 1621 (1956). Structure and configuration: Kupchan, Narayanan, ibid. 81, 1913 (1959). Comparative toxicity: O. Krayer et al., J. Pharmacol. Exp. Ther. 82, 167 (1944).
Properties
Crystals from methanol, mp 221.5-223°. [α]D25 +4.5° (95% ethanol); [α]D16 +23.1° (c = 1.13 in 10% acetic acid). Sol in chloroform, methanol, ethanol, acetone, water; slightly sol in ether. LD50 i.v. in mice: 139.0 mg/kg (Krayer).Derivative
3-Acetate.C29H45NO9; mol wt 551.67.
C 63.14%, H 8.22%, N 2.54%, O 26.10%.
Properties
Needles from ether, mp 219-221°. [α]D23 +10° (c = 1.05 in pyridine).Derivative
16-Acetate.C29H45NO9; mol wt 551.67.
C 63.14%, H 8.22%, N 2.54%, O 26.10%.
Properties
Crystals from chloroform, mp 225-227°. [α]D23 19° (c = 0.93 in pyridine).Derivative
3,4,7,15,16-Pentaacetate.C37H53NO13; mol wt 719.82.
C 61.74%, H 7.42%, N 1.95%, O 28.90%.